RS21 is seeking a Senior IT Support Specialist to serve as the organization's senior-level owner of internal IT operations, endpoint health, and technology service delivery. This is a high-ownership, highly autonomous role for an experienced IT professional who can operate independently across the full scope of RS21's technology environment, from day-to-day helpdesk resolution and device lifecycle management through compliance support, systems administration, and continuous process improvement.
The Senior IT Support Specialist will work in partnership with the Information Security Manager, taking a leading role in maintaining endpoint security baselines, supporting ISO 27001, SOC 2, and FedRAMP compliance requirements across the IT environment, and ensuring that identity, access, and device management practices are consistently enforced and audit ready. This role brings both the technical depth to resolve complex issues and the organizational maturity to build scalable processes and contribute meaningfully to RS21's security and operational posture.
This role is well suited for a seasoned IT professional who combines deep hands-on expertise with the strategic awareness to identify systemic gaps, recommend improvements, and elevate the overall technology experience for a distributed, mission-driven workforce. At RS21, IT is not a background function. The Senior IT Support Specialist is a visible, trusted, and consequential partner to every team in the organization.
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Serve as the first and primary point of contact for all IT helpdesk requests submitted through Jira Service Management, triaging, prioritizing, and resolving tickets in accordance with defined service level targets.
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Diagnose and resolve complex hardware, software, connectivity, and application issues across macOS, Windows, and mobile platforms, serving as the senior technical escalation point for difficult or recurring issues before engaging external vendors.
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Provide clear, timely, and professional communication to end users throughout the lifecycle of every support request, from acknowledgment through resolution and follow-up.
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Maintain thorough documentation of all incidents, resolutions, and workarounds in the Jira knowledge base to build an organizational library of repeatable fixes and reduce recurring ticket volume.
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Monitor helpdesk queues proactively, identifying trends in issue frequency or type that signal systemic problems requiring root cause intervention.
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Deliver support across remote and hybrid work environments, utilizing remote access tools and video communication to assist distributed staff effectively.
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Administer and maintain RS21's mobile device management environment using Jamf Pro for macOS and iOS devices, including configuration profile management, policy enforcement, software deployment, and compliance reporting.
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Manage Windows device enrollment, configuration, and policy enforcement through Microsoft Intune or equivalent MDM tooling integrated with Microsoft Entra ID.
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Perform system imaging, provisioning, and configuration of new and replacement devices, ensuring all endpoints are deployed in a standardized, security-hardened state consistent with RS21's baseline requirements.
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Manage the full device lifecycle from procurement and enrollment through reassignment and secure decommission, maintaining accurate records at every stage.
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Own the patch management program for the endpoint fleet, establishing cadence, testing protocols, and rollout procedures in coordination with the Information Security Manager to ensure timely remediation of critical vulnerabilities with minimal user disruption.
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Support zero-touch or near-zero-touch deployment workflows through Automated Device Enrollment (ADE) via Apple Business Manager and equivalent Windows autopilot processes.
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Own and maintain RS21's IT asset inventory, tracking all hardware, software licenses, peripherals, and accessories from acquisition through end of life using asset management tooling integrated with Jamf and Entra ID.
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Conduct regular physical and digital audits of the asset inventory to ensure accuracy, identify unaccounted or unmanaged devices, and flag assets approaching end of support or license renewal.
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Manage software license entitlements across the organization's SaaS portfolio, identifying underutilized licenses, flagging compliance gaps, and coordinating renewals with procurement and finance.
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Maintain organized records of hardware warranty information, vendor contacts, and support agreements to enable efficient resolution of hardware failures.
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Prepare regular inventory and asset utilization reports for leadership to support informed purchasing, budgeting, and refresh cycle decisions.
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Execute all IT components of the employee onboarding process, including device provisioning, account creation and access provisioning in Microsoft Entra ID, application licensing, and delivery of a fully configured workstation on or before the employee's first day.
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Coordinate with People Operations and hiring managers to gather role-specific access requirements ahead of start dates, ensuring new employees have the tools and permissions they need from day one.
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Lead the IT offboarding process for departing employees, including timely account deactivation and access revocation across all systems, device retrieval and secure data wipe, license reclamation, and documentation of the offboarding record.
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Develop and maintain clear, accessible onboarding guides and self-service resources that help new employees navigate RS21's technology environment independently.
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Continuously improve onboarding and offboarding workflows based on feedback, incident patterns, and evolving organizational needs, with the goal of delivering a consistently seamless experience for every employee.
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Administer user identities, groups, conditional access policies, and role-based access controls within Microsoft Entra ID (formerly Azure Active Directory), maintaining the principle of least privilege across the organization.
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Serve as a peer technical partner to the Information Security Manager in implementing, monitoring, and maintaining security controls across the endpoint environment, including MFA enforcement, disk encryption, endpoint detection and response policies, and device compliance baselines.
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Support security compliance requirements relevant to RS21's business, including ISO 27001, SOC 2, HIPAA, FedRAMP, or other applicable frameworks, by ensuring endpoint configurations, access records, and audit trails are current and accurate.
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Lead first-response actions on security alerts related to endpoint health, access anomalies, or policy violations, applying senior judgment to triage and remediate issues, and escalating to the Information Security Manager with full context and recommended action.
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Assist in the preparation and evidence gathering for internal and external security audits, providing accurate device inventory data, access logs, and configuration compliance reports.
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Promote a security-aware culture across RS21 by educating staff on safe computing practices, phishing awareness, and acceptable use policies in a clear and approachable way.
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Administer and maintain RS21's core IT systems including Microsoft 365 (Exchange Online, Teams, SharePoint, OneDrive), Google Workspace where applicable, and collaboration and productivity tools used across the organization.
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Manage IT service management workflows within Atlassian Jira Service Management, including queue configuration, SLA definitions, ticket categorization, and reporting dashboards.
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Monitor system health, uptime, and performance of key IT infrastructure components, driving resolution through vendor engagement or independent troubleshooting and escalating to the Information Security Manager only when security implications require joint decision-making.
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Maintain accurate and current documentation of IT systems, configurations, processes, and vendor relationships in Confluence or an equivalent knowledge management platform.
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Evaluate and recommend tools, integrations, or process improvements that reduce manual IT effort, improve the employee technology experience, and strengthen RS21's overall IT operations posture.
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Support the procurement process for new hardware and software by researching options, gathering quotes, and coordinating with finance and operations for approval and purchase.
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Bachelor’s degree in information technology, Computer Science, or a related field, or equivalent practical experience.
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6+ years of experience in IT support, systems administration, or a related role, with at least 3 years in a senior-level or lead capacity within a technology, data, or professional services company.
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Hands-on experience with Jamf Pro for macOS and iOS endpoint management, including policy creation, configuration profiles, software deployment, and compliance reporting.
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Proficiency with Microsoft Entra ID (Azure Active Directory) for identity and access management, including user provisioning, group management, conditional access, and MFA configuration.
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Experience with Atlassian Jira Service Management or a comparable ITSM platform for helpdesk ticket management, documentation, and SLA tracking.
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Working knowledge of Microsoft 365 administration, including Exchange Online, Teams, SharePoint, OneDrive, and Intune.
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Demonstrated experience performing system imaging, device provisioning, and endpoint configuration for both macOS and Windows environments.
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Familiarity with IT asset management practices and tooling, including maintaining accurate hardware and software license inventories.
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Understanding of endpoint security principles including patch management, disk encryption, MFA enforcement, and device compliance baselines.
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Strong written and verbal communication skills, with the ability to translate technical issues clearly for non-technical users and provide a consistently professional support experience.
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Highly organized, self-directed, and capable of managing multiple open issues simultaneously while maintaining responsiveness and service quality.
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Demonstrated ability to identify process gaps, design scalable IT workflows, and drive continuous improvement in service delivery quality and operational efficiency.
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Experience mentoring junior IT staff or serving as a senior technical resource for less experienced colleagues.
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Experience supporting IT operations in a remote-first or fully distributed workforce environment.
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Familiarity with Apple Business Manager (ABM) and automated device enrollment (ADE) workflows for zero-touch provisioning.
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Experience supporting security compliance frameworks such as ISO 27001, SOC 2, HIPAA, FedRAMP, or NIST 800-171 in an endpoint management context.
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Knowledge of Okta, Duo, or other identity and access management or MFA platforms used alongside Entra ID.
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Familiarity with Atlassian Confluence for IT knowledge base management and documentation.
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Experience with endpoint detection and response (EDR) tools such as CrowdStrike Falcon, Microsoft Defender for Endpoint, or similar platforms.
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CompTIA A+, CompTIA Security+, Microsoft Certified: Modern Desktop Administrator Associate, or Jamf Certified Associate/Technician certification.
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Exposure to ITIL service management principles and familiarity with applying ITIL-aligned practices to helpdesk operations.
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Experience participating in or supporting IT security audits, including evidence collection and control documentation.
